1. Field of the Invention
This invention relates to 2-substituted-1-(omega-aminoalkoxy)benzenes which are pharmacologically active as antidepressants.
2. Description of the Prior Art
L. C. Cheney et al, J. Am. Chem. Soc., Vol. 71, 60-64 (1949) describes several diphenylmethanes containing a substituent at the 2-position, including 2-dimethylaminoethoxy, 2-diethylaminoethoxy, 2-morpholinoethoxy, 2-(1-piperidyl)ethoxy, 2-isopropylaminoethoxy, 3-(1-piperidyl)propoxy, 3-dimethylaminopropoxy and 3-dibutylaminopropoxy.
That reference also indicates that 2-(2-aminoethoxy)diphenylmethanes and 2-(3-aminopropoxy)diphenylmethanes have antihistaminic and local anesthetic activity in animals. Similarly, U.S. Pat. Nos. 2,703,324, 2,966,518, 2,534,236 and 2,768,207 disclose 2-omega-aminoalkoxydiphenylmethanes such as 2-(3-diethylaminopropyl)diphenylmethane and 2-(5-dimethylaminopentyl)diphenylmethane. J. Med. Chem., Vol. 9, page 806 (1966) discloses 2-(4-dimethylaminobutoxy)diphenylmethane.
Journal Pharm. Soc. Japan, Vol. 89, pages 1078-1084 (1969) and Vol. 89, pages 1417-1425 (1970), Japanese Patents published for opposition Nos. 9937/1970 and 9938/1970 disclose 2-(omega-dialkylaminoethoxy)diphenyl ethers, 2-(omega-cycloiminoethoxy)diphenyl ethers, 2-(omega-dialkylaminopropoxy)diphenyl ethers and 2-(omega-cycloiminopropoxy)diphenyl ethers, each benzene ring being optionally substituted by chloro or methyl.
Chemical Abstracts, Vol. 72, 3152 y and Vol. 73, P 76852 disclose 2-(3-diethylaminopropoxy)diphenyl ether.
Chemical Abstracts, Vol. 45, page 577 (1951) discloses 2-(diethylaminoethoxy)diphenyl sulfide.
U.S. Pat. No. 2,703,324 discloses 2-(2-diethylaminoethoxy)diphenylmethylmethane.
U.S. Pat. Nos. 2,187,723 and 3,213,140 disclose 2-omega-aminoalkoxybiphenyl such as 2-(2-pentylaminoethoxy)biphenyl. Similarly, British Pat. No. 521,575 discloses 2-omega-aminoalkoxybiphenyl such as 2-(3-dimethylaminopropoxy)biphenyl, 2-(2-aminoethoxy)biphenyl and 2-(2-ethylaminoethoxy)biphenyl. However, none of these prior art compounds is disclosed as having antidepressant activity.